Nowadays I feel new school especially digital is the way to go. You can get far more value for your buck and the possibilities are endless. However If you do have the money and understand the machines old school synths can be unique and bring a certain presence you might not be able to fully recreate digitally.
I think that old school synthesizers have such a unique sound to offer. There's something about the user experience that is aesthetically pleasing, and yet modern synthesizers offer so many unique features and customizations to really dial in the specific sounds you enjoy. Overall, I would say that modern synthesizers are what I prefer to play!
Have no clear idea about how any of the hardware of 2000 sound. Mostly had PCM synthesis of the early 90's Korgs, Rolands, Kawais and sampler hardware i never got a Triton or never, the oldest and only analog thing i owned was a Korg MS-20 and a Rhodes.
Now i just roll thumbs and play with a soundcanvas and a Korg N364, that i dream doing a patcheditor for i also got a RA-95 midi arranger that i have not started to play with,.
I don't get the real feeling with VST or software samplers i must say.
I also think that the early soundcards like SB AWE and GUS added some analog flavour to the software samplers of the time, that is just not there with a modern soundcard. I guess they had some preamps even if lousy that added something that is just not there in the digital mix. I used to have sampler on the Soundblaster AWE and record on the GUS until i got a PCI machine in mid 90s.
Both for me. I have instruments of every decade from the 70s to today. My studio is a complete mix. In the way of retro I have half a dozen 70s/80s analogue synths and couple of digital ones from the 90s. Hmmm, I've now had my Pro-One for ~40 years. Then I've got more modern, digital synths. I recently got a Microfreak and just added an Electro 6.
To perform outside the house, I tend to mostly use the modern, digital synths: FA-06, VR-09, Sledge, Nord.